Bis(tercarbazole) pyrene and tetrahydropyrene derivatives: Photophysical and electrochemical properties, theoretical modeling, and OLEDs

Bilal R. Kaafarani, Tarek H. El-Assaad, William A. Smith, Sean M. Ryno, Felix Hermerschmidt, Jeffrey Lyons, Digambara Patra, Brigitte Wex, Emil J.W. List-Kratochvil, Chad Risko, Stephen Barlow, Seth R. Marder

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


2,7-Bis(3,3′′,6,6′′-tetra(tert-butyl)-9′H-9,3′:6′,9′′-tercarbazol-9-yl)-4,5,9,10-tetrahydropyrene (3) and 2,7-bis(3,3′′,6,6′′-tetra(tert-butyl)-9′H-9,3′:6′,9′′-tercarbazol-9-yl)pyrene (4), along with a model compound, 3,3′′,6,6′′-tetra(tert-butyl)-9′-(4-(tert-butyl)phenyl)-9′H-9,3′:6′,9′′-tercarbazole (6), have been synthesized using microwave-assisted palladium-catalyzed coupling and compared to analogous 3,6-di(tert-butyl)carbazol-9-yl species (1, 2, and 5). Time-dependent density functional theory (TDDFT) calculations reveal absorption with quadrupolar (ter)carbazole-to-bridge CT character for 1-4. Compound 4 is unusual in showing dual fluorescence in a number of solvents; the longer wavelength feature of which is markedly more solvatochromic than the bands of the other compounds. Following the observed three oxidations on the TCz model compound 6, compounds 3 and 4 can be electrochemically reversibly oxidized to hexacations with four oxidation and three oxidation steps in a 2:2:1:1 and a 2:2:2 current ratio, respectively. Tercarbazole derivatives 3 and 4 have been used as the emissive layers of simple solution-processed few-layer organic light-emitting diodes.

Original languageEnglish
Pages (from-to)5009-5018
Number of pages10
JournalJournal of Materials Chemistry C
Issue number17
StatePublished - 2019

Bibliographical note

Funding Information:
This work was supported by the University Research Board (URB) of the American University of Beirut, the Lebanese National Council for Scientific Research (CNRS), and the Kamal A. Shair CRSL. B. R. K. and B. W. thank the Arab Fund Scholarship Program for financial support. S. R. M. thanks the Alexander Humboldt Foundation for support. The work at the University of Kentucky was supported by the Department of the Navy, Office of Naval Research, ONR Award No. N00014-16-1-2985. Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the University of Kentucky Information Technology Department and Center for Computational Sciences (CCS). The authors are grateful for this support.

Publisher Copyright:
© 2019 The Royal Society of Chemistry.

ASJC Scopus subject areas

  • Chemistry (all)
  • Materials Chemistry


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